Sofia Coppola

OF FAME:__2007. “I thought it was fun and flattering; as a kid I admired stylish ladies like Diana Vreeland, so it was fun to be thought of in that way.”

ON HER STYLE: “Trying to be chic when I can get it together.”

ENSEMBLE: “A dress I had from the Louis Vuitton Cruise collection last year.”

Painted from life in the Windsor Suite of the Ritz Paris on May 31, 2012.

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The Duchess of Windsor, who famously decreed that a lady could never be too rich or too thin, felt, on the other hand, that it was possible to be too “Best-Dressed.” In the late 50s, the impeccable Duchess, after being named 15 times to the International Best-Dressed List, asked Eugenia Sheppard, fashion editor of the New York Herald Tribune, to do something about the uncomfortable redundancy. Sheppard conferred with P.R. powerhouse Eleanor Lambert, the list’s founder, and the redoubtable duo solved the problem by establishing the Best-Dressed List Hall of Fame. The first group of inductees, announced in 1959, included not only the Duchess but also Countess Mona von Bismarck (a nine-time winner), Claudette Colbert, Babe Paley, Consuelo Vanderbilt Balsan, and Queen Elizabeth II. By telegram, Lambert congratulated each paragon of elegance, noting that they had now achieved “permanent recognition” for “distinguished taste in dress.”

Since that long-ago moment, 385 more luminaries—including men, who were welcomed into the Hall of Fame in 1968—have been elevated to the list’s loftiest empyrean. To be eligible, a candidate first must be elected to the regular list at least three times. From the Hall of Fame registry, Vanity Fair this year taps five outstandingly chic individuals who continue, in some cases decades after their initiation, to personify, “without ostentation,” as Eleanor Lambert insisted, the I.B.D.L. ideal.